Journal of a Beginning Sissy

Today was the day. After years of secretly watching feminization and sissy videos. I decided to stop being a sissy about buying sissy things and go get some panties.

It was a nerve wracking experience. At first I went to stores in the next town over, but they were all ridiculously busy. I got nervous and left each store after pacing around the make-up section like a creeper. I never even made it to the panty aisle.

Dejected I headed home feeling like a failure. I know you're thinking, why don't I just order through Amazon and avoid the shame. Well, its because I'm separated from my wife due to work. We still are happily married with joint accounts, but live in different states. She would notice an Amazon order and question the purchase. Cash and in person is my only option. So far I have saved a couple hundred in cash to get me started in dressing. I'm definitely on a budget. I can't believe how expensive everything is... $10 for cheap foundation no brush included. Arggh!

So I'm driving home, and I remember this ghetto Family Dollar store near my apartment. No one I know would shop there, because it is in a really bad neighborhood. I stopped there once to get some frozen burritos on the way home and a crack whore offered to blow me for $20. I didn't have enough cash on me, so I declined. I would like to think I would have said no if I had the $20, but now I'm getting off topic.

I pull into the Family Dollar, and walk in with my shoulders back and head held high. I'm determined no matter how busy it is, I'm at least purchasing something. I don't know these people and I don't care. I walk in and quickly find the make-up section. They have a very small selection, but to me it's huge! I have absolutely no idea what I should get and I'm afraid to touch anything.

I'm in the aisle for only a few minutes and a store clerk walks up to me. Seriously, Family Dollar isn't known for customer service, and today is the day a clerk decides to ask me if I need help? WTF!

I tell her I don't need help. But she is persistent. She asks if my wife sent me to buy her a few things... Shoulders back, head held high.. Fuck it I don't know these people and I don't care. I look her dead in the eye and say No I'm shopping for myself.

Apparently there aren't many crossdressers frequenting this store. Her jaw dropped, and she literally asked me why and what I was going to do with it. I wanted to reply I was going to get dressed up and fuck my ass with a cucumber, but I'm not that bold. Instead I just told her I was going to put it on and feel pretty. She congratulated me for being so open and honest and then stood there watching me for what seemed like ages before walking away.

I found some foundation, eye shadow, fake lashes, lipstick and a brush after she left and walked to the panty aisle of the store. Unfortunately a family was there picking up some things for their daughter. I am not looking for panties with a family standing right next to me, so I wander the store till they leave. Wandering the store with an arm full of make-up for everyone to see made me feel like a complete perv. It was a rough experience to wait out. Finally the family left and I was able to move in.

Getting the aisle to myself was a relief. I came prepared. I knew my size and was going to grab a pack and head directly to the check-out. Problem was they didn't have my size hanging up neatly on the rack for a quick snatch and grab. Instead I had to fish through the pile of panties that had fallen off the rack to the bottom shelf.

After fishing through the panty package pile for ages; I found two packs in my size. I found a pack of high rise briefs and a pack of hipsters in my size. I choose the hipsters and bee-lined it for the register.

The cashier was the same clerk who approached me in the make-up section. Now I don't just have make-up, I have panties as well. My nerves were fried, but I was almost done. Fuck it I don't know these people and I don't care.

I place my items on the counter. She literally fans them all out for everyone behind me to see. I mentally tell myself I'm being self conscious and to calm down. As she rings each item ups she looks up at me and forces eye contact. I'm getting irritated, but I'm not backing down so I stare right back at her refusing to look away.

I know I'm not being silly now. This is an official pissing contest. As she rings each item up rather than placing it in a bag she sets it back on the counter all nice and neat for all to see. When she is done, she tells me the total and I hand her some bills.

Waiting for her to give me my change and bag my items took forever. It was like she was intentionally moving in slow motion. As she was bagging my purchase up she loudly asks if I do shows dressed up, because she would like to come. I reply No it's more of a private thing. Hoping she would take a hint.

She didn't. Instead she goes on that it is great that we live in a country where guys can express themselves, and if I want to wear pretty pink panties I should.

My ears were on fire. They had to have been bright red from embarrassment at this point. I took my bag politely thanked her and turned to leave.

As I walked away from the counter I could hear the guy behind disgustedly mutter Fag. Fuck it, I don't know these people and I don't care. I finally got some stuff to dress up a little with.

Total spent approx. $40... Not everything at Family Dollar is a dollar.

Feelings: I feel good. Overall a positive experience. It was a little confrontational, but it felt good to actually vocalize to someone that I do this. The embarrassment was unwanted but if I am honest it was a turn on, especially at the end. I'll probably use that store again for make-up. I wish they had a bigger selection of clothes. They mainly have pjs and workout women's clothing. I like yoga pants but I want dresses, skirts, blouses, and heels.